The Boston and Lowell Railroad was opened in 1835. The Woburn branch was opened in 1844. The Horn Pond Branch Railroad was a short freight-only branch off the Woburn Branch to the ice houses at Horn Pond Woburn. The line was built at the request of the Boston Ice Company and trains ran only during ice cutting season. The line opened in 1854 and was abandoned in 1919. In 1955 the railroad overpass in Winchester center was started. Commuter trains ran to Woburn center until 1981.
Winchester was served by 4 trolley lines radiating out from Winchester center. The trolleys were managed by the Eastern Mass Street Railway Company.
Winchester to Woburn via Main Street
Winchester to Stoneham via Washington and Forest Streets
Winchester to Arlington Center via Church and Cambridge Streets